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Triphenylamine derivatives, and preparation method and application thereof

A technology of derivatives and triphenylamine, applied in the fields of triphenylamine derivatives and their preparation and application, can solve the problems of limited application of materials and little fluorescence intensity, and achieves the effects of good cyclability, simple synthesis method and convenient preparation of devices

Active Publication Date: 2014-09-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the reversible piezochromic phenomenon reported so far is mainly the change of the fluorescent color of the material under the action of external force, but rarely the change of the fluorescence intensity; in addition, the reversible temperature is generally greater than 100°C, (J.Am.Chem. Soc.2010, 132, 13675-13683) will greatly limit the application of such materials

Method used

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  • Triphenylamine derivatives, and preparation method and application thereof
  • Triphenylamine derivatives, and preparation method and application thereof
  • Triphenylamine derivatives, and preparation method and application thereof

Examples

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Embodiment 1

[0036]1.63g (12mmol) of p-methoxybenzaldehyde, 1.96g (10mmol) of p-bromonitrile benzyl and 0.06g (1mmol) of sodium methoxide were dissolved in 30ml of chromatographic ethanol. The reaction was stirred at room temperature for 4 h until a large number of solid particles were present to terminate the reaction. Then put it into -20 DEG C refrigerator overnight and then filter, and the filter cake was rinsed with ethanol three times to obtain a white powder, that is, 2.84 g of brominated stilbene nitrile intermediate (IV), with a yield of 90%. The structural confirmation of the substance is characterized as follows: 1 H NMR (500MHz, CDCl 3 ) δ (ppm) 7.78(s, 1H), 7.48(d, J=7.5Hz, 2H), 7.39(d, J=7.5, 2H), 7.34(d, J=7.5, 2H), 6.91(d, J=7.5, 2H), 3.82(s, 1H); 13 C NMR (500MHz, CDCl 3 ); δ161.3, 141.2, 132.7, 131.8, 131.0, 126.1, 119.7, 114.5, 106.6, 56.0; MS (EI): m / e 313.0 (M + ).

Embodiment 2

[0038] Dissolve 1.09 g (8 mmol) of p-methoxybenzaldehyde, 1.96 g (10 mmol) of p-bromonitrile benzyl and 0.03 g (0.5 mmol) of sodium methoxide in 30 ml of chromatographically pure ethanol. The reaction was stirred at room temperature for 3 h until a large number of solid particles were present to terminate the reaction. Then put it into -20 DEG C refrigerator overnight and then filter, and the filter cake was rinsed with ethanol three times to obtain a white powder, that is, 2.19 g of brominated stilbene nitrile intermediate (IV), with a yield of 90%.

Embodiment 3

[0040] Weigh the stilbene nitrile intermediate (IV) 1.57g (5mmol) of the brominated synthesis above, 1.73g (6mmol) of triphenylamine 4-boric acid, and 0.11g (0.1mmol) of tetrakis (triphenylphosphine) palladium. To a solution of 50 mL of toluene / 30 mL of tetrahydrofuran, an aqueous solution of sodium carbonate (2.0 M, 3 mL) was added. Under a nitrogen atmosphere, the temperature was raised to 90° C. for 36 h. The reaction solution was cooled, the solvent was distilled off under reduced pressure, extracted three times with chloroform, the organic phases were combined, washed with saturated sodium carbonate and brine, and finally dried over anhydrous magnesium sulfate. Filtration, the filtrate was concentrated under reduced pressure, and the residue was subjected to thin-layer chromatography with silica gel column chromatography, and the volume ratio of petroleum ether / chloroform was eluted with a mixed solvent of 150 / 1, and the solvent was evaporated under reduced pressure to ob...

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Abstract

The invention discloses triphenylamine derivatives, and a preparation method and application thereof. The structure of the triphenylamine derivatives is disclosed as Formula (I). The preparation method comprises the following steps: (1) carrying out Knoevenagel condensation reaction on anisaldehyde and p-bromobenzyl cyanide to generate a bromated distyrene nitrile intermediate; and (2) carrying out Suzuki reaction on the bromated distyrene nitrile intermediate and 4-(diphenylamino)phenylboronic acid to generate the triphenylamine derivatives disclosed as Formula (I). The triphenylamine derivatives (I) disclosed by the invention have reversible-force-stimulated fluorescence switching performance, thus, can be used as a reversible-force-stimulated fluorescence switching material, and can be used in the fields of fluorescence switching, sensors, memories, display and the like.

Description

(1) Technical field [0001] The invention relates to a triphenylamine derivative, a preparation method thereof and an application as a reversible force stimulating fluorescent switch material, which is suitable for sensors, anti-counterfeiting, storage and displays. (2) Background technology [0002] The phenomenon that the fluorescence color changes when the material is subjected to mechanical force is called piezochromism, and substances with piezochromism have at least two stable or metastable accumulation modes affected by pressure. After being stimulated by a force, the internal force of the molecule changes, resulting in a change in the molecular packing method, which makes the material change from one ordered structure to another ordered or partially ordered or disordered structure, and the photophysical properties of the material change with time. change. Then, after being treated with heating and solvents, the accumulation mode of the molecules will return to the or...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/43C07C253/30C09K9/02
Inventor 张诚孙璟玮张玉建林超颖欧阳密胡彬
Owner ZHEJIANG UNIV OF TECH
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